Ammonia → N,N-Dimethyl-3-((naphthalen-1-yl)oxy)-3-(thiophen-2-yl)propan-1-amine

HRID 2388361Notes

Reaction equation

HRID 2388361 reaction equation
C(O)(=O)C(O)=O.[CH3:7][N:8]([CH3:28])[CH2:9][CH2:10][CH:11]([O:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1)[C:12]1[S:13][CH:14]=[CH:15][CH:16]=1.O.N>C1CCCCC1>[CH3:28][N:8]([CH3:7])[CH2:9][CH2:10][CH:11]([O:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1)[C:12]1[S:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 19830102116817-12-0

Product 1

HCID 11573192N,N-Dimethyl-3-((naphthalen-1-yl)oxy)-3-(thiophen-2-yl)propan-1-amine

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

Racemic N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine oxalate salt (5, HA=oxalic acid) (15 gm) was suspended in mixture of water (100 ml) and cyclohexane (50 ml). This suspension was basified with aqueous ammonia and then layers were separated. The cyclohexane layer was washed with water and concentrated under reduced pressure to give oily mass of (±)-N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine free base (6a+6b). Yield: 10 gm.

Workup

  1. customlayers were separated
  2. washThe cyclohexane layer was washed with water
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f113d865e64c40f399e87816733dfe94
Source dataset
uspto-grants-2012_09
Patent number
US08269023B2

Reaction notes

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